Movies Like (500) Days of Summer

If you liked (500) Days of Summer (2009), a comedy and drama movie directed by Marc Webb, here are 20 movies with a similar feel, based on TMDB's recommendations. Each one links to its cast, trailer and where it's streaming.

1
Catch and Release (2006)
★ 5.9/10Also comedy and drama
For a grieving fiancée, learning to love again requires the help of her late love's three best friends.
2
Hitch (2005)
★ 6.6/10Also comedy and drama
Dating coach Alex 'Hitch' Hitchens mentors a bumbling client, Albert, who hopes to win the heart of the glamorous Allegra Cole. While Albert makes progress, Hitch faces his own romantic setbacks when proven techniques…
3
He Said, She Said (1991)
★ 5.9/10Also comedy and drama
Womanising, right-wing Dan Hanson and quiet, liberal Lorie Bryer work for the Baltimore Sun. Rivals for the job of new writer of a vacant column, the paper ends up instead printing their very different opinions…
4
The Wrong Paris (2025)
★ 6.7/10Also romance and comedy
Dawn thinks she's joining a dating show in Paris, France, only to land in Paris, Texas. She has an exit plan — until sparks fly with the cowboy bachelor.
5
One Day (2011)
★ 7.4/10Also drama and romance
After spending the night together on the eve of their college graduation, Dexter and Emma are shown each year on the same date to see where they are in their lives. They are sometimes together, and sometimes not.
6
Young Adult (2011)
★ 5.8/10Also comedy and drama
A divorced writer from the Midwest returns to her hometown to reconnect with an old flame, who's now married with a family.
7
The Big Picture (1989)
★ 5.9/10Also comedy and romance
Hollywood beckons for recent film school grad Nick Chapman, who is out to capitalize on the momentum from his national award-winning student film. Studio executive Allen Habel seduces Nick with a dream deal to make his…
8
Yoh! Bestie (2026)
★ 6.2/10Also romance and comedy
Thando is perpetually unlucky in love, but when her bestie returns from his travels with a fiancée in tow, she's forced to face a new emotion — jealousy.
9
Another Year (2010)
★ 7/10Also drama and comedy
During a year, a very content couple approaching retirement are visited by friends and family less happy with their lives.
10
Café Society (2016)
★ 6.4/10Also comedy and drama
The story of a young man who arrives in Hollywood during the 1930s hoping to work in the film industry, falls in love, and finds himself swept up in the vibrant café society that defined the spirit of the age.
11
Which Brings Me to You (2023)
★ 6.3/10Also romance and comedy
Two romantic burnouts, Jane and Will, are immediately drawn to each other at a mutual friend’s wedding. After a disastrous hookup in the coatroom, the two spend the next 24 hours together, trading candid confessions of…
12
New York, I Love You (2008)
★ 6/10Also comedy and drama
New York, I Love You delves into the intimate lives of New Yorkers as they grapple with, delight in and search for love. Journey from the Diamond District in the heart of Manhattan, through Chinatown and the Upper East…
13
Valentine's Day (2010)
★ 5.9/10Also comedy and romance
Intertwining couples and singles in Los Angeles break-up and make-up based on the pressures and expectations of Valentine's Day.
14
A California Christmas: City Lights (2021)
★ 6.6/10Also romance and comedy
Follows Callie and Joseph one year after they fell in love, now running a dairy farm and winery, but their romance is threatened when business and family obligations call Joseph back to the city.
15
Author! Author! (1982)
★ 6/10Also comedy and drama
While facing the stress of his original play being produced on Broadway, playwright Ivan Travalian deals with having to raise his son, his stepdaughters, and his stepsons.
16
Is This Thing On? (2025)
★ 6.6/10Also comedy and drama
As their marriage quietly unravels, Alex faces middle age and an impending divorce, seeking new purpose in the New York comedy scene while Tess confronts the sacrifices she made for their family—forcing them to…
17
Shag (1989)
★ 6.2/10Also comedy and drama
Summer of 1963. Carson is getting married to her boyfriend so her friends Melaina, Pudge and Luanne take her to Myrtle Beach for one last irresponsible weekend.
18
Sidewalks of New York (2001)
★ 6.1/10Also comedy and drama
The film follows the marital and dating lives of three men and three women who unknowingly form a tangled web of relationships. Interspersing "man on the street" interviews with scenes from the six characters' lives…
19
Licorice Pizza (2021)
★ 6.9/10Also drama and comedy
The story of Gary Valentine and Alana Kane growing up, running around and going through the treacherous navigation of first love in the San Fernando Valley, 1973.
20
Home Again (2017)
★ 6.1/10Also comedy and drama
Life for a single mom in Los Angeles takes an unexpected turn when she allows three young guys to move in with her.